Trifluoroacetic acid → HCID 59432444, compound

HRID 507124Notes

Reaction equation

HRID 507124 reaction equation
C(OC([N:8]1[C:21]2[C:13](=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=2)[C@@H:12]([N:22]([CH2:41][C:42]2[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[C:44]([C:52]([F:55])([F:54])[F:53])[CH:43]=2)[C:23]2[N:24]=[N:25][N:26]([CH2:28][CH2:29][N:30]3[C:38](=[O:39])[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[C:31]3=[O:40])[N:27]=2)[CH2:11][CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl.O>[F:50][C:48]([F:49])([F:51])[C:46]1[CH:47]=[C:42]([CH:43]=[C:44]([C:52]([F:53])([F:54])[F:55])[CH:45]=1)[CH2:41][N:22]([C@@H:12]1[C:13]2=[CH:14][C:15]3[CH2:16][O:17][CH2:18][C:19]=3[CH:20]=[C:21]2[NH:8][CH2:9][CH2:10][CH2:11]1)[C:23]1[N:24]=[N:25][N:26]([CH2:28][CH2:29][N:30]2[C:31](=[O:40])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]2=[O:39])[N:27]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59432459HCID 59432459, compound

Product 1

HCID 59432444HCID 59432444, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-9-((3,5-Bis-trifluoromethyl-benzyl)-{2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-2H-tetrazol-5-yl}-amino)-1,3,6,7,8,9-hexahydro-2-oxa-5-aza-cyclohepta[f]indene-5-carboxylic acid tert-butyl ester (Example 106, Step 1) (0.39 mmol) in dichloromethane (5 mL), add trifluoroacetic acid (2 mL). After stirring at room temperature for 3 h, quench the reaction with concentrated sodium carbonate, dilute with dichloromethane (20 mL), and water (20 mL). Separate the organic phase and wash the aqueous with dichloromethane (2×10 mL). Dry the combined organics over sodium sulfate, filter, and remove solvent under vacuum. Chromatograph the product over silica gel eluting with ethyl acetate/hexane (10-50%) to provide the title intermediate as a colorless foam. MS (ES+): 730 (M+59).

Workup

  1. customquench
  2. customthe reaction with concentrated sodium carbonate
  3. customSeparate the organic phase
  4. washwash the aqueous with dichloromethane (2×10 mL)
  5. dry with materialDry the combined organics over sodium sulfate
  6. filtrationfilter
  7. customremove solvent under vacuum

Sources & evidence

ORD record
ord-f11a52b155d847d1877cea4f5a3cc9d3
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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